Synthesis of quinolines via sequential addition and I2-mediated desulfurative cyclization

Mingming Yang; Yajun Jian; Weiqiang Zhang; Huaming Sun; Guofang Zhang; Yanyan Wang; Ziwei Gao

doi:10.1039/D1RA06976D

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Synthesis of quinolines via sequential addition and I₂-mediated desulfurative cyclization†

Mingming Yang,^a Yajun Jian,

^a Weiqiang Zhang,

^a Huaming Sun,^a Guofang Zhang,

^a Yanyan Wang

*^a and Ziwei Gao

*^ab

Author affiliations

* Corresponding authors

^a Key Laboratory of Applied Surface and Colloid Chemistry, Xi'an Key Laboratory of Organometallic Material Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710119, P. R. China
E-mail: zwgao@snnu.edu.cn, yyw@snnu.edu.cn

^b A School of Chemistry & Chemical Engineering, Xinjiang Normal University, Urumqi 830054, P. R. China

Abstract

An efficient one-pot approach for the synthesis of quinolines from o-aminothiophenol and 1,3-ynone under mild conditions is disclosed. With the aid of ESI-MS analysis and parallel experiments, a three-step mechanism is proposed—a two-step Michael addition–cyclization condensation step leading to intermediate 1,5-benzothiazepine catalyzed by zirconocene amino acid complex Cp₂Zr(η¹-C₉H₁₀NO₂)₂, followed by I₂-mediated desulfurative step.

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Article information

DOI: https://doi.org/10.1039/D1RA06976D
Article type: Paper
Submitted: 17 Sep 2021
Accepted: 28 Nov 2021
First published: 06 Dec 2021
This article is Open Access

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RSC Adv., 2021,11, 38889-38893

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Synthesis of quinolines via sequential addition and I₂-mediated desulfurative cyclization

M. Yang, Y. Jian, W. Zhang, H. Sun, G. Zhang, Y. Wang and Z. Gao, RSC Adv., 2021, 11, 38889 DOI: 10.1039/D1RA06976D

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